(S)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butane-1,3-diol

Base Information

Chemical Name:(S)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butane-1,3-diol
CAS No.:884338-26-5
Molecular Formula:C₁₉H₃₀O₅
Molecular Weight:338.444
Hs Code.:

Synonyms:(S)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butane-1,3-diol

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Chemical Property of (S)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butane-1,3-diol

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Technology Process of (S)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butane-1,3-diol

There total 4 articles about (S)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butane-1,3-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

: 884338-24-3
(E)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-but-2-en-1-ol

: 884338-26-5
(S)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butane-1,3-diol

Guidance literature:: (E)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-but-2-en-1-ol; With titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate; In dichloromethane; at -20 ℃; for 3h;

With sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; at -10 ℃; for 3h;
DOI:10.1016/j.tetlet.2006.01.130

Reference yield:

: ((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-acetaldehyde

: 884338-26-5
(S)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butane-1,3-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: CH₂Cl₂ / 4 h / 20 °C

2.1: DIBAL-H / CH₂Cl₂ / 0.33 h / -78 °C

3.1: D-(-)-DIPT; Ti(O-iPr)4; TBHP / CH₂Cl₂ / 3 h / -20 °C

3.2: 92 percent / Red-Al / tetrahydrofuran / 3 h / -10 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; In dichloromethane; 3.1: Sharpless epoxidation;
DOI:10.1016/j.tetlet.2006.01.130

Reference yield:

: 2-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethanol

: 884338-26-5
(S)-4-((4S,5R,6R)-6-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butane-1,3-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

2.1: CH₂Cl₂ / 4 h / 20 °C

3.1: DIBAL-H / CH₂Cl₂ / 0.33 h / -78 °C

4.1: D-(-)-DIPT; Ti(O-iPr)4; TBHP / CH₂Cl₂ / 3 h / -20 °C

4.2: 92 percent / Red-Al / tetrahydrofuran / 3 h / -10 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxalyl dichloride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; In dichloromethane; 1.1: Swern oxidation / 4.1: Sharpless epoxidation;
DOI:10.1016/j.tetlet.2006.01.130